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Title: Palladium-Catalyzed Enantioselective α-Arylation of α-Fluoroketones
Authors: Jiao, Zhiwei
Beiger, Jason J.
Jin, Yushu
Ge, Shaozhong
Zhou, Jianrong Steve
Hartwig, John F.
Keywords: Palladium catalysis
Issue Date: 2016
Source: Jiao, Z., Beiger, J. J., Jin, Y., Ge, S., Zhou, J. S., & Hartwig, J. F. (2016). Palladium-Catalyzed Enantioselective α-Arylation of α-Fluoroketones. Journal of the American Chemical Society, 138(49), 15980-15986.
Series/Report no.: Journal of the American Chemical Society
Abstract: The transition-metal-catalyzed α-arylation of carbonyl compounds is a widely practiced method for C–C bond formation. Several enantioselective versions of this process have been reported, but intermolecular, enantioselective coupling reactions of aryl electrophiles with α-fluoro carbonyl compounds have yet to be disclosed. We report enantioselective coupling of aryl and heteroaryl bromides and triflates with α-fluoroindanones catalyzed by palladium complexes of a BINOL-derived monophosphine and Segphos, respectively. The enolates were generated directly from α-fluoroindanones in the presence of potassium phosphate base during the reactions. We also report that reactions of α-fluorotetralones occur in high yields and enantioselectivities when conducted with enolates generated by elimination of trifluoroacetate from trifluoromethyl β-diketone hydrates. These reactions were catalyzed by palladium complexes of the commercially available bisphosphine Difluorphos. Thus, the formation of enantioenriched α-aryl-α-fluoroketones can be readily achieved by C–C bond formation when the appropriate palladium catalyst and α-fluoro enolate precursor were used.
ISSN: 0002-7863
DOI: 10.1021/jacs.6b09580
Schools: School of Physical and Mathematical Sciences 
Rights: © 2016 American Chemical Society. This is the author created version of a work that has been peer reviewed and accepted for publication by Journal of the American Chemical Society, American Chemical Society. It incorporates referee’s comments but changes resulting from the publishing process, such as copyediting, structural formatting, may not be reflected in this document. The published version is available at: [].
Fulltext Permission: open
Fulltext Availability: With Fulltext
Appears in Collections:SPMS Journal Articles

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